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JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02800
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This study presents a intramolecular C(sp3)-H annulation of functionalized 2,6-lutidines catalyzed by an organocalcium hydride. The reaction provides a streamlined approach for the synthesis of tetrahydro-1,5naphthyridines and hexahydropyrido[3,2-b]azocines derivatives with high efficiency and broad substrate scope. The isolation and structural characterization of a calcium alkyl complex confirms its role as the catalytic intermediate.
This work reports an intramolecular C(sp3)-H annulation of functionalized 2,6-lutidines catalyzed by an organocalcium hydride [{(DIPPnacnac)CaH(thf)}2] (DIPPnacnac = CH{(CMe)(2,6-iPr2-C6H3N)}2). This reaction constitutes a streamlined approach for producing a new family of tetrahydro-1,5naphthyridines and hexahydropyrido[3,2-b]azocines derivatives in good to excellent yields with high atom efficiency and broad substrates scope. A calcium alkyl complex was isolated from the stoichiometric reaction between calcium hydride and the substrate through deprotonation, which was structurally characterized and confirmed as the catalytic intermediate.
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